Dyestuff of the naphthophenazine series cbtained from 3-arylamino-1-3-naphthsultam compounds



Patented Aug. 6, 1929.

'f UNITED STATES PATENT oFFic'E.

WILHELI NEWER, OF LEVEBKO'SEN, AND THE-ODOR ROCKER, OI WIESDORF, GER- MANY, ASSIGNOBS T GENERAL ANIL A CORPORATION OF DELAWARE.

IKE WORSE, INC., 01' NEW YORK, N. Y.,

."DY ESTUI'I-OF THE KAPETEOPEENAZINE SERIES OBTAINED FROM S-ABYLAKINO-l-S v 1 'ZIAPBZTHSULTAM COMPOUNDS.

In Application filed July 21, 1920, Serial lo. 124,090, and in Germany July 28,1885. I

Our invention consists in the production naphthophenazine d estufis' of the safranine type which'are erived from 3- arylamino-l-S-naphthsultam compounds and in 6 processes of makingthe same.

' The production of safranine type dyestufis containing the naphthophenazine nucleus wherein R and R, standfor hydrogen alkyl or aryl has been variously described. The reactions leading to the dyestuffs containing this nucleus consist mainlyin condensing 1-3-dinitroso-aminobenzene compounds, or joint oxidation of 1-3-di-er lamino-naphthalene compounds with p-d1aminobenzene compounds.

Our invention consists in applying these reactions leading to the formation of the most likely the following nucleus arylamino-naphthalene compounds with p-.

wherein R "and R, stand for hydrogen, alkyl, aryl' or aralkyl, R for hydrogen or alkyl which we call the naphthsultam-phenazine 4 nucleus. The 3-arg'lamino-1-8-naphthsultam compounds use ul in our novel process are described in our 00- nding application Serial No. 124,091, filed .liily 21, 1926. They are 0b tamed by condensing 1-8-naphthsultam-3- sulfonic acid compounds with arylamines.

Amongst the arylamino-naphthsultam compounds we prefer to use the 3-a-rylamino-1- 8-naphth'sultam-6 sulfonic acids for the production of our novel dyestuffs. Also 3-arylamino-l-8-naphthsultam-6-sulfonic acids in which the na hthsultam nitrogen is substituted by an a kyl group have been found to yield valuable dyes.

Our novel naphthsultam-phenazine dyestufis'arechemically characterized by containing the naphthsultam-phenazine nucleus .ILI @Aryl ,wherein R and R stand for hydrogen, alkyl, 811% aralkyl, R for hydrogen or alkyl.

e}: are in the dry state or in form of 7 their ydrochlorides dark colored powders with metallic lustre, soluble in water and con centrated sulfuric acid with intense colors. Reducing agents react with them with forma- 4 tion of colorless leuco compounds from which an oxidation regenerates the original dyestuffs.

They dye wool from acid baths exceedingly level and clear red to violet shades. 4, The following examples will further illlls; v

trate our invention, the parts being by weight, but it is understood that our invention is not limited to the particular materials or reacting conditions mentioned therein.

Example 1.276 parts 3-phenylamino-1-8- naphthsultam-G-sulfonic acid are dissolved in alcohol and 280 parts p-nitroso-dimethylaniline hydrochloride added. This solution is heated for a short time on the water bath whereby the p-nitrosodimethylaniline partly 2 mi. NH

and then allowed to cool. The dyestufl crystallizes; it is filtered OE and washed with alcohol. It is in the dry statea dark crystalline powder with a cuprous lustre, soluble in water with a reddish-violet color and dyes wool from an acid bath beautiful, level, reddish-violet shades.

Example 2.390 parts 3-(4-tolylamino)- 1-8-naphthsultaIn-6-sulfonic acid are dis- NICE):

HIV

It is a dark crystalline powder with a cuprous lustre, soluble in water with a reddish-violet color and dyes wool from an acid bath violet, very level shades.

Example 3.-The dyestufi obtained from 3- phenylamino 1 8 naphthsultam-G-sulfonio reacts as oxidizing agent according to the following equation:

NH, \l .HCl 3H3O N (one,

acid and p-phenylenediamine-sulfonic acid, having most probably the formula soin x nsoin. III N H:

is a crystalline powder with a bronze-like lustre, soluble in water witha red color and in concentrated sulfuric acid with a brownishyellow color. It dyes wool from an acid bath level, very clear red shades.

' Eat-ample 4.The dyestufl' obtained from 3- phenylamino 8-N-methyl-1-8-naphthsultamfi-sulfonic acid and 4-amin0-dimethyl-aniline-3- sulfonic acid is in form of its hydrochloride, having most probably the formula:

soin

a violet powder with bronze-like l ustre, soluble in water with a violet color, in concentrated sulfuric acid "with a green color. It dyes wool from an acid bath brilliant violet, level shades.

I radio We claim 1. As new products naphthsultam-phenazine dyestufl's corresponding to the formula:

wherein R and R stand for an of the grou hydrogen, alkyl, ar 1 and ara yl, R stan s for h drogen or aliiyl, z designates an acid I and 3 stands for hydrogen or a monovalent substituent, which are dark crystalline powders with metallic lustre, soluble in concentrated'sulfuric acid and in water with intense colors, and dye wool from an acid bath red to violet level shades.

2. As new products naphthsultam-phenazine dyestuffs corresponding to the formula:

dry] 1 mist. 1,723,199.

formula and insert instead zine dyestufl's corresponding to the formula:

BOQH

N\ i so I I) \N N one,

1'; (ill wherein R stands for hydrogen or alkyl, which are dark crystalline powders with metallic lustre soluble in concentrated sulfuric acid and in water with intense colors, and dye wool from an acid bath red to violet level shades.

4. As a new product a naphthsultamphenazine dyestufi corresponding to the formula:

SOIH

which is a violet powder with bronze-like lustre soluble in Water with a violet color and in concentrated sulfuric acid with a green color, dyeing Wool from an acid bath brilliant violet level shades.

In testimony whereof we afiix our signatures.

WILHELM NEELMEIER] THEODOR NOOKEN.

Granted-Augusto, 1929, w'

v WILHELM NEELMEIER ET AL.

It is hereby certified that error appears in the printed specificatiomoi the above "numbered patent requiring correction as follows: Page 1, lines 65 to 70, strike out the and that the said Letters Patent should be read with this that the..- seme may conform to the record of the case inthe Patent Ofiice. Signed. and sealed thia8th day of'Qtttobor, A. D. 1929.

. M. J. MOORE, Acting Commissioner PM. 

